Sightseeing
From quirky tours to can’t-miss landmarks, sightseeing in The Florida Keys is anything but ordinary - on island or at sea. Hop on a trolley or the iconic Conch Train, set sail on a charter, or wander museums filled with history, art, and stories you couldn’t make up if you tried. Key West’s haunted tours add a spooky thrill, while scenic drives and hidden stops up and down the island chain reveal the Keys’ offbeat charm. These listings connect you with the guides, tours, and attractions that turn “just looking around” into a true island adventure.
Filters
Key West
Second Generation Fishing Charters
We Fish Key West — your local charter partner for top offshore, reef, and backcountry fishing adventures.
Key West
My Ohana Fishing Charters
My Ohana Fishing & Charters offers sport fishing, snorkeling, reef & sandbar tours, and custom boat adventures in Key West.
Key West
Florida Keys Flight Academy Key West
Florida Keys Flight Academy — flight training and scenic tours in Marathon, where aspiring pilots and adventure seekers soar over the stunning Florida Keys.
Islamorada
Coastal Outfitters Sport Fishing Charters
Coastal Outfitters offers customized fishing charters and sunset cruises in Islamorada, delivering relaxed, captained outings tailored to your preferences.
Key West
Rusty's Bucket Charters
Rusty's Bucket Charters offers private fishing trips, snorkeling, sunset cruises, and sandbar adventures aboard a 24' Sea Hunt center console. Led by Captain Russ, they provide a hands-on experience for up to six guests, with trips tailored to your preferences.
Key West
Fun in the Sun
Fun In The Sun Key West is the home of the original Key West sandbar charter, offering private captained boat charters, bareboat rentals, fishing trips, snorkeling, sunset cruises, boat bar crawls, golf cart rentals, and vacation rentals out of Stock Island Yacht Club with a 5-star TripAdvisor rating.
Key West
Dolphin Safari Charters Key West
Dolphin Safari Charters offers small-group dolphin watching, snorkeling and private boat charters departing from Stock Island near Key West.
Islamorada
Blackbeard Private Charters
Blackbeard Private Charters offers personalized boat excursions in the Florida Keys, including trips to the Islamorada Sandbar, snorkeling at Alligator Reef, sightseeing, and sunset cruises.
Marathon
Nautica Watersports
Thrilling jet ski adventures and serene sunset rides in Marathon, Florida.
Key Largo
Cruisin’ Tikis Key Largo
Cruisin’ Tikis Key Largo offers quirky tiki-bar boat cruises—ranging from fun daytime outings to romantic sunset sails and seasonal night tours—departing dockside at Snook’s Bayside in Key Largo.
Key West
Classic Harbor Line Key West
Sail Key West offers unforgettable sunset and specialty cruises aboard the elegant Schooner America 2.0.
Marathon
Manic Sportfishing
Manic Sportfishing is a top-rated Florida Keys fishing charter in Marathon offering private offshore, reef, and family-friendly fishing trips with experienced captains and premium boats.
Islamorada
Allergic to Land Charters
Discover Islamorada's waters with Captain Sue—snorkel, sunset, eco tours.
Islamorada
Pretty Work Charters
Pretty Work Charters — full-service fishing charters in Islamorada, FL, where experienced crews and flexible boats deliver unforgettable Florida Keys adventures.
Key Largo
Pirate's Choice Sailing Vessel
Sail Key Largo’s pirate ship for sunset & snorkel adventures
